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In 2010, while touring with the supergroup the Dukes of September Rhythm Revue alongside Steely Dan's Donald Fagen and iconic blue-eyed soul man Boz Scaggs, singer Michael McDonald performed "Don't Mess Up a Good Thing," a 1965 Fontella Bass and Bobby McClure song the former Doobie Brothers singer hadn't revisited since he was 14.

"It's one of those songs you could never foresee a reason to do again," he told reporters on a conference call Wednesday to discuss the Dukes' second jaunt, a 40-show tour which kicks off June 20th in St. Louis. The tour, McDonald says, gives himself and his fellow music icons the chance to unearth such rarities – obscure R&B, blues and jazz tunes. "It's a big exercise in letting go,” he said.

Scaggs admitted the forthcoming tour, during which the trio will be supported by Fagen's Steely Dan band, will take each member out of their comfort zone. "It's kind of terrifying at first," he said. "But it does a lot for the three of our spirits just as musicians. It's kind of a rejuvenating experience."

McDonald agreed. "When you're a solo artist for a few years, there's a part of you that longs for that journeyman status. This situation fulfills that urge for all of us. It's like something after school – going to the sandlot, playing ball or something."

One of the main challenges of the tour, Scaggs explained, is deciding how obscure the Dukes can go, song-wise. The three musicians have been exchanging emails over the past few weeks suggesting potential tunes to cover, a process that won't be ironed out until upcoming rehearsals. "There are definitely songs that come on the list that seem too obscure," Scaggs said. "One of the objectives is to choose (non-traditional) material that the audience has perhaps heard, but with a twist in the arrangement or twist in the vocal delivery. It can be pretty funny sometimes where this might go if we let ourselves run completely free with it."

Both men were guarded about particular songs fans can expect to hear on the tour, only noting a reworking of Gladys Knight's version of "I Heard It Through The Grapevine," complete with backing female singers ("That will be fun for the audience to hear that version live," McDonald said. "That's the first version we all heard"), and a potential Lovin' Spoonful medley. There are also talks about some form of tribute to the Band’s Levon Helm. On their last go-round the Dukes unveiled a vocal tribute to the Band, but Scaggs is aware this time a Band-related performance would take on far greater significance. "The Band was a great inspiration to Mike's and my generation," he said.

McDonald and Scaggs are also aware many fans would like the Dukes to record an album. While leaving the possibility open, right now the two musicians say they are simply trying to get excited about touring with each other and Fagen.

"I'm sure by the end of these 40 cities we're gonna know each other better, and who knows what could come out," Scaggs said.

Scaggs and McDonald, in addition to their work with the Dukes, are working on their own respective projects: Scaggs is currently finishing an album of new material he hopes to record in September, and McDonald is working on a cover-song project with his son, Dylan.

"We started picking songs for each other," McDonald said of the family project. "He picked a Radiohead song for me. I loved it. A father and son who normally can't get along in the studio picking songs for each other – we thought that would be hilarious."